Chapter 7, Amines Flashcards
What 2 different properties to amines have?
Basic and nucleophilic
What are amines and why do they act the way they do?
They act as nucleophiles because of the lone pair on the Nitrogen
What gives amines basic properties?
The lone pair can accept a proton.
What does the base strength depend on?
How available the lone pair is
What is the base strength of ethylamine compared to ammonia?
It is a stronger base than ammonia because of the positive inductive effect the C2H5 group has
What is the base strength of phenylamine compared to ammonia?
It is a weaker base than ammonia due to the negative inductive effect the benzene ring and delocalised electrons have
What cause amines to have nucleophilic properties?
It can donate an electron pair
What do nucleophiles attack?
They attack electron deficient areas
What functional group do amines commonly attack?
Haloalkanes to give a mixture of products
If express ammonia is used then ___ is the major product formed
Primary amine
If excess ammonia isn’t used then what happens?
The primary amine can act as a nucleophile to form a secondary amine. This continues until a quaternary salt has been formed
What are the 2 ways amines can be formed?
Reaction if ammonia with haloalkanes.
Reduction of nitriles.
Reduction of aromatic nitro compounds.
What are the reagents for the reaction of ammonia with haloalkanes?
Haloalkanes with EXCESS ammonia in ethanol
What are the reagents needed for the reduction of nitriles?
Nitrile, hydrogen and nickel catalyst
What are the advantages of reduction of nitriles to produce amines?
Gives a better yield and no other products are formed
